Methods for the selective detection of alkyne-presenting molecules and related compositions and systems

Abstract

Provided herein are methods for selectively detecting an alkyne-presenting molecule in a sample and related detection reagents, compositions, methods and systems. The methods include contacting a detection reagent with the sample for a time and under a condition to allow binding of the detection reagent to the one or more alkyne-presenting molecules possibly present in the matrix to the detection reagent. The detection reagent includes an organic label moiety presenting an azide group. The binding of the azide group to the alkyne-presenting molecules results in emission of a signal from the organic label moiety.

The invention claimed is: 
     
       1. A method for selectively detecting an alkyne-presenting molecule in an untreated sample, the method comprising:
 contacting a detection reagent with the untreated sample for a time and under a condition for click chemistry to allow binding of the detection reagent to the one or more alkyne-presenting molecules possibly present in the untreated sample, the contacting performed in absence of a treatment of the untreated sample that introduces the one or more alkyne-presenting molecules into the untreated sample prior to the contacting; 
 wherein the detection reagent comprises an organic label moiety presenting an azide group and wherein binding of the azide group to the alkyne-presenting molecules results in emission of a signal from the organic label moiety. 
 
     
     
       2. The method of  claim 1 , wherein the untreated sample is an aqueous or organic solution. 
     
     
       3. The method of  claim 1 , wherein the organic label moiety comprises a fluorescent or pre-fluorescent moiety. 
     
     
       4. The method of  claim 1 , wherein the signal is a fluorescent signal. 
     
     
       5. The method of  claim 1 , wherein the detection reagent has formula I or II: 
       
         
           
           
               
               
           
         
       
       wherein:
 R 1 -R 6  are independently selected from the group consisting of H, N 3 , substituted or unsubstituted C 1 -C 8  alkyl, substituted or unsubstituted amino such that at least one of R 1 -R 6  is N 3 ; 
 Y 1  is selected from the group consisting of H, substituted or unsubstituted C 1 -C 8  alkyl, substituted or unsubstituted aryl or heteroaryl, alkoxy, or polyalkoxy; 
 R 1a -R 6a  and R 1b -R 6b  are independently selected from the group consisting of H, N 3 , substituted or unsubstituted C 1 -C 8  alkyl, substituted or unsubstituted amino, and substituted or unsubstituted oxygen such that at least one of R 1a -R 6a  is N 3  and at least one of R 1b -R 6b  is N 3 ; and 
 X 1  is O, N, NH, N-alkyl, or N-aryl. 
 
     
     
       6. The method of  claim 5 , wherein Y 1  is selected from the group consisting of formulas III-VI: 
       
         
           
           
               
               
           
         
       
     
     
       7. The method of  claim 1 , wherein the detection reagent has formula VII: 
       
         
           
           
               
               
           
         
       
       wherein:
 R 1 -R 6  are independently selected from the group consisting of H, N 3 , substituted or unsubstituted C 1 -C 8  alkyl, substituted or unsubstituted amino, and substituted or unsubstituted oxygen such that at least one of R 1 -R 6  is N 3 . 
 
     
     
       8. The method of  claim 1 , wherein the untreated sample is selected from blood, urine, drinking water, and agricultural irrigation water.